CZ7598A3 - Deriváty kyseliny fenyloctové, postup a meziprodukty k jejich výrobě a jejich použití jako přípravek proti škůdcům a fungicidy - Google Patents

Info

Publication number

CZ7598A3

CZ7598A3 CZ9875A CZ7598A CZ7598A3 CZ 7598 A3 CZ7598 A3 CZ 7598A3 CZ 9875 A CZ9875 A CZ 9875A CZ 7598 A CZ7598 A CZ 7598A CZ 7598 A3 CZ7598 A3 CZ 7598A3

Authority

CZ

Czechia

Prior art keywords

compounds

formula

compound

methyl

cyclopropyl

Prior art date

1995-07-27

Links

• Espacenet
• Global Dossier
• Discuss

• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract description 41
• 238000000034 method Methods 0.000 title claims abstract description 23
• 241000607479 Yersinia pestis Species 0.000 title claims description 14
• 238000002360 preparation method Methods 0.000 title claims description 10
• 239000000543 intermediate Substances 0.000 title claims description 8
• 239000000417 fungicide Substances 0.000 title description 10
• 239000000575 pesticide Substances 0.000 title description 3
• 239000001257 hydrogen Substances 0.000 claims abstract description 91
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 91
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 73
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 38
• 125000003118 aryl group Chemical group 0.000 claims abstract description 35
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims abstract description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 17
• 150000003839 salts Chemical class 0.000 claims abstract description 14
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 11
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
• 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 7
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 6
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 4
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 3
• -1 cyano, nitro, hydroxy, mercapto, amino, carboxyl Chemical group 0.000 claims description 1704
• 150000001875 compounds Chemical class 0.000 claims description 1598
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 585
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 142
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 84
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 67
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 125000001424 substituent group Chemical group 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 239000000203 mixture Substances 0.000 claims description 34
• 125000004122 cyclic group Chemical group 0.000 claims description 33
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
• 125000004104 aryloxy group Chemical group 0.000 claims description 28
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 27
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 125000005110 aryl thio group Chemical group 0.000 claims description 22
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 19
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
• 241000233866 Fungi Species 0.000 claims description 12
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
• 241001465754 Metazoa Species 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 7
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 239000000463 material Substances 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 5
• 230000000269 nucleophilic effect Effects 0.000 claims description 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 239000000654 additive Substances 0.000 claims description 2
• 150000001450 anions Chemical class 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
• 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 2
• 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
• 125000004438 haloalkoxy group Chemical group 0.000 claims 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract description 8
• 238000004519 manufacturing process Methods 0.000 abstract description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
• 125000006193 alkinyl group Chemical group 0.000 abstract 2
• 125000006725 C1-C10 alkenyl group Chemical group 0.000 abstract 1
• 239000013067 intermediate product Substances 0.000 abstract 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 473
• 125000001309 chloro group Chemical group Cl* 0.000 description 97
• 125000001246 bromo group Chemical group Br* 0.000 description 77
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 51
• 239000003921 oil Substances 0.000 description 50
• 239000000243 solution Substances 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• 241000196324 Embryophyta Species 0.000 description 32
• 239000004480 active ingredient Substances 0.000 description 29
• KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 description 29
• 125000004432 carbon atom Chemical group C* 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 238000006243 chemical reaction Methods 0.000 description 26
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 22
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 18
• 229910052799 carbon Inorganic materials 0.000 description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 description 18
• 125000004430 oxygen atom Chemical group O* 0.000 description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
• 229960003424 phenylacetic acid Drugs 0.000 description 17
• 239000003279 phenylacetic acid Substances 0.000 description 17
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 16
• 125000004434 sulfur atom Chemical group 0.000 description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 14
• 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 14
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 14
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
• 238000012360 testing method Methods 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• 238000005160 1H NMR spectroscopy Methods 0.000 description 10
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000003995 emulsifying agent Substances 0.000 description 9
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 8
• 238000002474 experimental method Methods 0.000 description 8
• 125000002950 monocyclic group Chemical group 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 239000003960 organic solvent Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 241000209140 Triticum Species 0.000 description 7
• 235000021307 Triticum Nutrition 0.000 description 7
• 239000013543 active substance Substances 0.000 description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 7
• 125000005514 but-1-yn-3-yl group Chemical group 0.000 description 7
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 125000003277 amino group Chemical group 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 239000002270 dispersing agent Substances 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• 238000003860 storage Methods 0.000 description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 5
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 5
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 5
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 5
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 5
• 240000007594 Oryza sativa Species 0.000 description 5
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 5
• 238000001035 drying Methods 0.000 description 5
• 238000010410 dusting Methods 0.000 description 5
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 5
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 4
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
• 125000005999 2-bromoethyl group Chemical group 0.000 description 4
• 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 4
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 4
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 4
• 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 4
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 206010061217 Infestation Diseases 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 235000007164 Oryza sativa Nutrition 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 125000005997 bromomethyl group Chemical group 0.000 description 4
• 235000013339 cereals Nutrition 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000004440 column chromatography Methods 0.000 description 4
• 238000002425 crystallisation Methods 0.000 description 4
• 230000008025 crystallization Effects 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• 150000002191 fatty alcohols Chemical class 0.000 description 4
• 230000002538 fungal effect Effects 0.000 description 4
• 230000000855 fungicidal effect Effects 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 125000005843 halogen group Chemical group 0.000 description 4
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 4
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 4
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 4
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 4
• 235000009566 rice Nutrition 0.000 description 4
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
• 235000012239 silicon dioxide Nutrition 0.000 description 4
• 159000000000 sodium salts Chemical class 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 235000013311 vegetables Nutrition 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 3
• NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
• RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 3
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 3
• 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
• 241001480061 Blumeria graminis Species 0.000 description 3
• 241000123650 Botrytis cinerea Species 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 3
• 125000003282 alkyl amino group Chemical group 0.000 description 3
• RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 3
• 235000012211 aluminium silicate Nutrition 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 3
• 150000001728 carbonyl compounds Chemical class 0.000 description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
• 239000004359 castor oil Substances 0.000 description 3
• 235000019438 castor oil Nutrition 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 238000011161 development Methods 0.000 description 3
• 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 3
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 3
• 238000011156 evaluation Methods 0.000 description 3
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
• 235000012054 meals Nutrition 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 3
• 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 3
• 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 3
• 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 3
• 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• 239000002689 soil Substances 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
• 239000002699 waste material Substances 0.000 description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
• NNQDMQVWOWCVEM-NSCUHMNNSA-N (e)-1-bromoprop-1-ene Chemical compound C\C=C\Br NNQDMQVWOWCVEM-NSCUHMNNSA-N 0.000 description 2
• CRPTXKKKIGGDBX-UHFFFAOYSA-N (z)-but-2-ene Chemical group [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 2
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 2
• ZIRGWUZHKJDYKT-UHFFFAOYSA-N 1,3-thiazole-2-carbonitrile Chemical compound N#CC1=NC=CS1 ZIRGWUZHKJDYKT-UHFFFAOYSA-N 0.000 description 2
• PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 2
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• YHRSRHKHEVJSBL-UHFFFAOYSA-N 4-chloro-1,2-thiazole Chemical compound ClC=1C=NSC=1 YHRSRHKHEVJSBL-UHFFFAOYSA-N 0.000 description 2
• DLRXEPREUKUZQO-UHFFFAOYSA-N 4-chloro-1,3-thiazole Chemical compound ClC1=CSC=N1 DLRXEPREUKUZQO-UHFFFAOYSA-N 0.000 description 2
• DWUPYMSVAPQXMS-UHFFFAOYSA-N 5-bromo-1,3-thiazole Chemical compound BrC1=CN=CS1 DWUPYMSVAPQXMS-UHFFFAOYSA-N 0.000 description 2
• BQRBAXFOPZRMCU-UHFFFAOYSA-N 5-chloro-1h-imidazole Chemical compound ClC1=CN=CN1 BQRBAXFOPZRMCU-UHFFFAOYSA-N 0.000 description 2
• 241000239223 Arachnida Species 0.000 description 2
• 244000025254 Cannabis sativa Species 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 241000191839 Chrysomya Species 0.000 description 2
• 241000931705 Cicada Species 0.000 description 2
• 241000254137 Cicadidae Species 0.000 description 2
• 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
• 229920000742 Cotton Polymers 0.000 description 2
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• 241000221785 Erysiphales Species 0.000 description 2
• 244000299507 Gossypium hirsutum Species 0.000 description 2
• 241000238631 Hexapoda Species 0.000 description 2
• 240000005979 Hordeum vulgare Species 0.000 description 2
• 235000007340 Hordeum vulgare Nutrition 0.000 description 2
• 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 2
• 241000256602 Isoptera Species 0.000 description 2
• 241001142635 Lema Species 0.000 description 2
• 241000257162 Lucilia <blowfly> Species 0.000 description 2
• 241001330975 Magnaporthe oryzae Species 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• 244000070406 Malus silvestris Species 0.000 description 2
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 2
• 241000244206 Nematoda Species 0.000 description 2
• 241000358422 Nephotettix cincticeps Species 0.000 description 2
• 244000046052 Phaseolus vulgaris Species 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
• 241001430696 Protis Species 0.000 description 2
• 241001123569 Puccinia recondita Species 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
• 235000011941 Tilia x europaea Nutrition 0.000 description 2
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 240000008042 Zea mays Species 0.000 description 2
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
• 239000000853 adhesive Substances 0.000 description 2
• 230000001070 adhesive effect Effects 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 229910052783 alkali metal Inorganic materials 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 125000003302 alkenyloxy group Chemical group 0.000 description 2
• 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
• 150000008052 alkyl sulfonates Chemical class 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• 235000021016 apples Nutrition 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
• 238000003556 assay Methods 0.000 description 2
• IWLXWEWGQZEKGZ-UHFFFAOYSA-N azane;zinc Chemical compound N.[Zn] IWLXWEWGQZEKGZ-UHFFFAOYSA-N 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
• 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 description 2
• 125000004663 dialkyl amino group Chemical group 0.000 description 2
• 125000004989 dicarbonyl group Chemical group 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 239000000428 dust Substances 0.000 description 2
• 235000013399 edible fruits Nutrition 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 150000002170 ethers Chemical class 0.000 description 2
• 239000003337 fertilizer Substances 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 150000004820 halides Chemical class 0.000 description 2
• 239000004009 herbicide Substances 0.000 description 2
• 125000004468 heterocyclylthio group Chemical group 0.000 description 2
• XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 208000015181 infectious disease Diseases 0.000 description 2
• HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
• 239000004571 lime Substances 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• 230000003211 malignant effect Effects 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 239000002808 molecular sieve Substances 0.000 description 2
• KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 description 2
• 125000006129 n-pentyl sulfonyl group Chemical group 0.000 description 2
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
• 150000002790 naphthalenes Chemical class 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 description 2
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
• 150000004760 silicates Chemical class 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 125000005017 substituted alkenyl group Chemical group 0.000 description 2
• 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
• 239000002023 wood Substances 0.000 description 2
• NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
• WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
• OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 1
• 125000006079 1,1,2-trimethyl-2-propenyl group Chemical group 0.000 description 1
• SJIORNBDYHDISC-UHFFFAOYSA-N 1,1-dichloropropa-1,2-diene Chemical compound ClC(Cl)=C=C SJIORNBDYHDISC-UHFFFAOYSA-N 0.000 description 1
• 125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
• 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
• 125000006061 1,2-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006034 1,2-dimethyl-1-propenyl group Chemical group 0.000 description 1
• 125000006062 1,2-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
• 125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
• 125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006066 1,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
• KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
• BSNIXNVMYNRRMG-UHFFFAOYSA-N 1,3-oxazole-5-carbonitrile Chemical compound N#CC1=CN=CO1 BSNIXNVMYNRRMG-UHFFFAOYSA-N 0.000 description 1
• XWXPRCDFFCVMNT-UHFFFAOYSA-N 1,3-thiazole-5-carbonitrile Chemical compound N#CC1=CN=CS1 XWXPRCDFFCVMNT-UHFFFAOYSA-N 0.000 description 1
• OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
• WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
• WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
• FBGKAFRWBNEYTR-UHFFFAOYSA-N 1-[2-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]ethyl]-1,2,4-triazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CCN1N=CN=C1 FBGKAFRWBNEYTR-UHFFFAOYSA-N 0.000 description 1
• YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
• 125000006073 1-ethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006080 1-ethyl-1-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000006036 1-ethyl-1-propenyl group Chemical group 0.000 description 1
• 125000006074 1-ethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006081 1-ethyl-2-methyl-1-propenyl group Chemical group 0.000 description 1
• 125000006082 1-ethyl-2-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000004736 1-ethyl-2-methylpropylthio group Chemical group C(C)C(C(C)C)S* 0.000 description 1
• 125000006037 1-ethyl-2-propenyl group Chemical group 0.000 description 1
• 125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
• 125000006044 1-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
• 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
• 125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
• 125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
• 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
• 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
• 125000006067 2,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006068 2,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006070 2,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
• OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 description 1
• YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
• PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
• UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 description 1
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
• VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
• OYMCMWPHMPODNK-UHFFFAOYSA-N 2-bromofuran Chemical compound BrC1=CC=CO1 OYMCMWPHMPODNK-UHFFFAOYSA-N 0.000 description 1
• BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
• 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
• 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
• OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
• WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
• 125000006076 2-ethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006077 2-ethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006078 2-ethyl-3-butenyl group Chemical group 0.000 description 1
• YXDXXGXWFJCXEB-UHFFFAOYSA-N 2-furonitrile Chemical compound N#CC1=CC=CO1 YXDXXGXWFJCXEB-UHFFFAOYSA-N 0.000 description 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000006040 2-hexenyl group Chemical group 0.000 description 1
• SNAKZQGNQQFDCV-UHFFFAOYSA-N 2-hydroxyimino-4-methylpentan-3-one Chemical compound CC(C)C(=O)C(C)=NO SNAKZQGNQQFDCV-UHFFFAOYSA-N 0.000 description 1
• CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
• ZMSIFDIKIXVLDF-UHFFFAOYSA-N 2-methyl-1,3,4-oxadiazole Chemical compound CC1=NN=CO1 ZMSIFDIKIXVLDF-UHFFFAOYSA-N 0.000 description 1
• IARMCEYEYXXEOS-UHFFFAOYSA-N 2-methyl-1,3-oxazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=CO1 IARMCEYEYXXEOS-UHFFFAOYSA-N 0.000 description 1
• 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 1
• 125000006045 2-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
• 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
• 125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
• 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
• 125000006056 2-methyl-4-pentenyl group Chemical group 0.000 description 1
• LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 1
• BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
• 125000005916 2-methylpentyl group Chemical group 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
• ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
• BGWBVEWXQAGTJL-UHFFFAOYSA-N 3,3,3-trichloropropanamide Chemical compound NC(=O)CC(Cl)(Cl)Cl BGWBVEWXQAGTJL-UHFFFAOYSA-N 0.000 description 1
• 125000006071 3,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006072 3,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
• FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
• GVLZUBFQBXXMJN-UHFFFAOYSA-N 3-(3-cyanophenyl)sulfonylbenzonitrile Chemical class C(#N)C=1C=C(C=CC=1)S(=O)(=O)C1=CC(=CC=C1)C#N GVLZUBFQBXXMJN-UHFFFAOYSA-N 0.000 description 1
• IWTBVKIGCDZRPL-LURJTMIESA-N 3-Methylbutanol Natural products CC[C@H](C)CCO IWTBVKIGCDZRPL-LURJTMIESA-N 0.000 description 1
• AJRGDQWFWJDYDP-UHFFFAOYSA-N 3-chloro-1,2-oxazole Chemical compound ClC=1C=CON=1 AJRGDQWFWJDYDP-UHFFFAOYSA-N 0.000 description 1
• NDSJUDPCTYRQFX-UHFFFAOYSA-N 3-chloro-1,2-thiazole Chemical compound ClC=1C=CSN=1 NDSJUDPCTYRQFX-UHFFFAOYSA-N 0.000 description 1
• KTCKIOYQNQQFLX-UHFFFAOYSA-N 3-chloro-1-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2h-pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C=C(Cl)C(N)N1C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O KTCKIOYQNQQFLX-UHFFFAOYSA-N 0.000 description 1
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000006041 3-hexenyl group Chemical group 0.000 description 1
• 125000006046 3-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
• 125000006054 3-methyl-3-pentenyl group Chemical group 0.000 description 1
• 125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 1
• 125000005917 3-methylpentyl group Chemical group 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• WTSXVIMLKCKWIW-UHFFFAOYSA-N 3h-1,3,4-oxadiazol-2-one Chemical compound O=C1NN=CO1 WTSXVIMLKCKWIW-UHFFFAOYSA-N 0.000 description 1
• CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
• OOTHTARUZHONSW-UHFFFAOYSA-N 4-[(2-chlorophenyl)hydrazinylidene]-3-methyl-1,2-oxazol-5-one Chemical compound CC1=NOC(=O)C1=NNC1=CC=CC=C1Cl OOTHTARUZHONSW-UHFFFAOYSA-N 0.000 description 1
• MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 1
• AIMLUMURKMKXLV-UHFFFAOYSA-N 4-chloro-1,3-oxazole Chemical compound ClC1=COC=N1 AIMLUMURKMKXLV-UHFFFAOYSA-N 0.000 description 1
• WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
• HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
• 125000006042 4-hexenyl group Chemical group 0.000 description 1
• KYQLTHDGZHQEME-UHFFFAOYSA-N 4-hydroxyimino-1-phenylpent-1-yn-3-one Chemical compound ON=C(C)C(=O)C#CC1=CC=CC=C1 KYQLTHDGZHQEME-UHFFFAOYSA-N 0.000 description 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• 125000006047 4-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
• UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
• XNONRNKAYRHZDJ-UHFFFAOYSA-N 5-bromo-1,2-thiazole Chemical compound BrC1=CC=NS1 XNONRNKAYRHZDJ-UHFFFAOYSA-N 0.000 description 1
• RZKVGQCJNANFDR-UHFFFAOYSA-N 5-chloro-1,2,4-thiadiazole Chemical compound ClC1=NC=NS1 RZKVGQCJNANFDR-UHFFFAOYSA-N 0.000 description 1
• IJPFBRONCJOTTA-UHFFFAOYSA-N 5-chloro-1h-pyrazole Chemical compound ClC1=CC=NN1 IJPFBRONCJOTTA-UHFFFAOYSA-N 0.000 description 1
• WJRKNLONLOMALV-UHFFFAOYSA-N 5-chloropyridine Chemical compound ClC1=C=NC=C[CH]1 WJRKNLONLOMALV-UHFFFAOYSA-N 0.000 description 1
• JGSMMBCVBWNILQ-UHFFFAOYSA-N 5-ethoxy-3-(trichloromethyl)-2h-thiadiazole Chemical compound CCOC1=CN(C(Cl)(Cl)Cl)NS1 JGSMMBCVBWNILQ-UHFFFAOYSA-N 0.000 description 1
• 125000006043 5-hexenyl group Chemical group 0.000 description 1
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
• 241000238876 Acari Species 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 241000238818 Acheta domesticus Species 0.000 description 1
• 241001014341 Acrosternum hilare Species 0.000 description 1
• 241000917225 Adelges laricis Species 0.000 description 1
• 241000256118 Aedes aegypti Species 0.000 description 1
• 241000256176 Aedes vexans Species 0.000 description 1
• 241001470785 Agrilus sinuatus Species 0.000 description 1
• 241001136249 Agriotes lineatus Species 0.000 description 1
• 241001031864 Agriotes obscurus Species 0.000 description 1
• 241000566547 Agrotis ipsilon Species 0.000 description 1
• 241000218475 Agrotis segetum Species 0.000 description 1
• 241001652650 Agrotis subterranea Species 0.000 description 1
• 241000449794 Alabama argillacea Species 0.000 description 1
• 241000223600 Alternaria Species 0.000 description 1
• 241000238682 Amblyomma americanum Species 0.000 description 1
• 239000004254 Ammonium phosphate Substances 0.000 description 1
• 241001256085 Anisandrus dispar Species 0.000 description 1
• 241000254175 Anthonomus grandis Species 0.000 description 1
• 241000625764 Anticarsia gemmatalis Species 0.000 description 1
• 241001600407 Aphis <genus> Species 0.000 description 1
• 241001425390 Aphis fabae Species 0.000 description 1
• 241001600408 Aphis gossypii Species 0.000 description 1
• 241000569145 Aphis nasturtii Species 0.000 description 1
• 241001095118 Aphis pomi Species 0.000 description 1
• 241000496365 Aphis sambuci Species 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 241001480752 Argas persicus Species 0.000 description 1
• 241001340598 Argyresthia conjugella Species 0.000 description 1
• 241000209134 Arundinaria Species 0.000 description 1
• 241000235349 Ascomycota Species 0.000 description 1
• 241001503477 Athalia rosae Species 0.000 description 1
• 241001174347 Atomaria Species 0.000 description 1
• 241000726102 Atta cephalotes Species 0.000 description 1
• 241000908426 Atta sexdens Species 0.000 description 1
• 241000580299 Atta texana Species 0.000 description 1
• 241001166626 Aulacorthum solani Species 0.000 description 1
• 241001367053 Autographa gamma Species 0.000 description 1
• 235000007319 Avena orientalis Nutrition 0.000 description 1
• 244000075850 Avena orientalis Species 0.000 description 1
• 241001490249 Bactrocera oleae Species 0.000 description 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 241001148506 Bitylenchus dubius Species 0.000 description 1
• 241000238662 Blatta orientalis Species 0.000 description 1
• 241000238657 Blattella germanica Species 0.000 description 1
• 241001629132 Blissus leucopterus Species 0.000 description 1
• 241000273318 Brachycaudus cardui Species 0.000 description 1
• 241001444260 Brassicogethes aeneus Species 0.000 description 1
• 241000982105 Brevicoryne brassicae Species 0.000 description 1
• 241001414201 Bruchus pisorum Species 0.000 description 1
• 241001388466 Bruchus rufimanus Species 0.000 description 1
• 241000398201 Bryobia praetiosa Species 0.000 description 1
• 241001491790 Bupalus piniaria Species 0.000 description 1
• YRBMPSDLVFXZAF-UHFFFAOYSA-N CC1=CC=C(C)O1.NC1CCCCC1 Chemical compound CC1=CC=C(C)O1.NC1CCCCC1 YRBMPSDLVFXZAF-UHFFFAOYSA-N 0.000 description 1
• 125000006519 CCH3 Chemical group 0.000 description 1
• 235000002566 Capsicum Nutrition 0.000 description 1
• 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
• 240000008384 Capsicum annuum var. annuum Species 0.000 description 1
• 241001350371 Capua Species 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• 241000255579 Ceratitis capitata Species 0.000 description 1
• REEFSLKDEDEWAO-UHFFFAOYSA-N Chloraniformethan Chemical compound ClC1=CC=C(NC(NC=O)C(Cl)(Cl)Cl)C=C1Cl REEFSLKDEDEWAO-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 241000255942 Choristoneura fumiferana Species 0.000 description 1
• 241001525905 Choristoneura murinana Species 0.000 description 1
• 241001124564 Choristoneura occidentalis Species 0.000 description 1
• 241001367803 Chrysodeixis includens Species 0.000 description 1
• 241000983417 Chrysomya bezziana Species 0.000 description 1
• 101150065749 Churc1 gene Proteins 0.000 description 1
• 240000007154 Coffea arabica Species 0.000 description 1
• 241000254173 Coleoptera Species 0.000 description 1
• 241001663470 Contarinia <gall midge> Species 0.000 description 1
• 241000304165 Cordylobia anthropophaga Species 0.000 description 1
• 240000008067 Cucumis sativus Species 0.000 description 1
• 235000009849 Cucumis sativus Nutrition 0.000 description 1
• 241000256059 Culex pipiens Species 0.000 description 1
• 241000371644 Curvularia ravenelii Species 0.000 description 1
• 241001635274 Cydia pomonella Species 0.000 description 1
• 241001090151 Cyrtopeltis Species 0.000 description 1
• 241000969022 Dasineura Species 0.000 description 1
• 241000084475 Delia antiqua Species 0.000 description 1
• 241001585354 Delia coarctata Species 0.000 description 1
• 241001414892 Delia radicum Species 0.000 description 1
• 241001631712 Dendrolimus pini Species 0.000 description 1
• 241000119571 Dermacentor silvarum Species 0.000 description 1
• 241001481695 Dermanyssus gallinae Species 0.000 description 1
• 241001012951 Diaphania nitidalis Species 0.000 description 1
• 241000879145 Diatraea grandiosella Species 0.000 description 1
• HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 description 1
• 241000255925 Diptera Species 0.000 description 1
• MTBZIGHNGSTDJV-UHFFFAOYSA-N Ditalimfos Chemical compound C1=CC=C2C(=O)N(P(=S)(OCC)OCC)C(=O)C2=C1 MTBZIGHNGSTDJV-UHFFFAOYSA-N 0.000 description 1
• 241000399948 Ditylenchus destructor Species 0.000 description 1
• 241000399949 Ditylenchus dipsaci Species 0.000 description 1
• 241001274799 Dreyfusia nordmannianae Species 0.000 description 1
• 241001274798 Dreyfusia piceae Species 0.000 description 1
• 241001088941 Dysaphis radicola Species 0.000 description 1
• 241001425477 Dysdercus Species 0.000 description 1
• 241001425472 Dysdercus cingulatus Species 0.000 description 1
• 241000353522 Earias insulana Species 0.000 description 1
• 241000400698 Elasmopalpus lignosellus Species 0.000 description 1
• 241000995027 Empoasca fabae Species 0.000 description 1
• 241000488563 Eotetranychus carpini Species 0.000 description 1
• 241001558857 Eriophyes Species 0.000 description 1
• 241000510928 Erysiphe necator Species 0.000 description 1
• 241001362584 Eupoecilia Species 0.000 description 1
• 241000515838 Eurygaster Species 0.000 description 1
• 241000098297 Euschistus Species 0.000 description 1
• 241000953886 Fannia canicularis Species 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 240000009088 Fragaria x ananassa Species 0.000 description 1
• 241000654868 Frankliniella fusca Species 0.000 description 1
• 241000927584 Frankliniella occidentalis Species 0.000 description 1
• 241000189591 Frankliniella tritici Species 0.000 description 1
• 241000223218 Fusarium Species 0.000 description 1
• 241001660201 Gasterophilus intestinalis Species 0.000 description 1
• 241000482313 Globodera ellingtonae Species 0.000 description 1
• 241001442497 Globodera rostochiensis Species 0.000 description 1
• 241000257323 Glossina morsitans Species 0.000 description 1
• 244000068988 Glycine max Species 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• DYMNZCGFRHLNMT-UHFFFAOYSA-N Glyodin Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCC1=NCCN1 DYMNZCGFRHLNMT-UHFFFAOYSA-N 0.000 description 1
• 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
• 241001232715 Granaria Species 0.000 description 1
• 241000257232 Haematobia irritans Species 0.000 description 1
• 241000256244 Heliothis virescens Species 0.000 description 1
• 241000258937 Hemiptera Species 0.000 description 1
• 241000498254 Heterodera glycines Species 0.000 description 1
• 241000379510 Heterodera schachtii Species 0.000 description 1
• 241000040487 Heterodera trifolii Species 0.000 description 1
• 241001466007 Heteroptera Species 0.000 description 1
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
• 241001153229 Hylobius Species 0.000 description 1
• 241000257303 Hymenoptera Species 0.000 description 1
• 241001508558 Hypera Species 0.000 description 1
• 241001508566 Hypera postica Species 0.000 description 1
• 241001531327 Hyphantria cunea Species 0.000 description 1
• 241000257176 Hypoderma <fly> Species 0.000 description 1
• 241000546120 Ips typographus Species 0.000 description 1
• 241001480843 Ixodes ricinus Species 0.000 description 1
• 241000400431 Keiferia lycopersicella Species 0.000 description 1
• 241001658023 Lambdina fiscellaria Species 0.000 description 1
• 241000255777 Lepidoptera Species 0.000 description 1
• 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
• 241000540210 Leucoptera coffeella Species 0.000 description 1
• 241001578972 Leucoptera malifoliella Species 0.000 description 1
• 235000019738 Limestone Nutrition 0.000 description 1
• 241000683448 Limonius Species 0.000 description 1
• 241000594031 Liriomyza sativae Species 0.000 description 1
• 241001520143 Liriomyza trifolii Species 0.000 description 1
• 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 1
• 241000012186 Litura Species 0.000 description 1
• 241001261104 Lobesia botrana Species 0.000 description 1
• 241001220357 Longidorus elongatus Species 0.000 description 1
• 241000193981 Loxostege sticticalis Species 0.000 description 1
• 241000736227 Lucilia sericata Species 0.000 description 1
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
• 241000501345 Lygus lineolaris Species 0.000 description 1
• 241001492180 Lygus pratensis Species 0.000 description 1
• 241000721703 Lymantria dispar Species 0.000 description 1
• 241001314285 Lymantria monacha Species 0.000 description 1
• 241001581015 Lyonetia clerkella Species 0.000 description 1
• 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
• 241000180172 Macrosiphum rosae Species 0.000 description 1
• 241000255685 Malacosoma neustria Species 0.000 description 1
• 241000171293 Megoura viciae Species 0.000 description 1
• 241001415013 Melanoplus Species 0.000 description 1
• 241001394950 Melanotus communis (Gyllenhal, 1817) Species 0.000 description 1
• 241000243787 Meloidogyne hapla Species 0.000 description 1
• 241000243786 Meloidogyne incognita Species 0.000 description 1
• 241000243785 Meloidogyne javanica Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
• 241000952627 Monomorium pharaonis Species 0.000 description 1
• 101100521345 Mus musculus Prop1 gene Proteins 0.000 description 1
• 241000581981 Muscina stabulans Species 0.000 description 1
• 241001477931 Mythimna unipuncta Species 0.000 description 1
• BZVZLHOMCKZNGR-UHFFFAOYSA-N N-(1-methoxyiminopropan-2-ylidene)hydroxylamine Chemical compound CON=CC(C)=NO BZVZLHOMCKZNGR-UHFFFAOYSA-N 0.000 description 1
• FZWXQUBVAAJPIQ-UHFFFAOYSA-N N-(3-methoxyimino-5-phenylpent-4-yn-2-ylidene)hydroxylamine Chemical compound CON=C(C#CC1=CC=CC=C1)C(C)=NO FZWXQUBVAAJPIQ-UHFFFAOYSA-N 0.000 description 1
• GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
• POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 1
• 241001671709 Nezara viridula Species 0.000 description 1
• VJAWBEFMCIINFU-UHFFFAOYSA-N Nitrothal-isopropyl Chemical compound CC(C)OC(=O)C1=CC(C(=O)OC(C)C)=CC([N+]([O-])=O)=C1 VJAWBEFMCIINFU-UHFFFAOYSA-N 0.000 description 1
• IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
• 241000375318 Nullosetigera Species 0.000 description 1
• 241001668536 Oculimacula yallundae Species 0.000 description 1
• 241000543819 Oestrus ovis Species 0.000 description 1
• 241000219830 Onobrychis Species 0.000 description 1
• 241001491877 Operophtera brumata Species 0.000 description 1
• 241001465803 Orgyia pseudotsugata Species 0.000 description 1
• 241000238887 Ornithodoros Species 0.000 description 1
• 241000238814 Orthoptera Species 0.000 description 1
• 241000975417 Oscinella frit Species 0.000 description 1
• 241001480756 Otobius megnini Species 0.000 description 1
• 241000488583 Panonychus ulmi Species 0.000 description 1
• 239000005662 Paraffin oil Substances 0.000 description 1
• 241000315044 Passalora arachidicola Species 0.000 description 1
• 241000562493 Pegomya Species 0.000 description 1
• 239000006002 Pepper Substances 0.000 description 1
• 241001517955 Phyllonorycter blancardella Species 0.000 description 1
• 241001227717 Phyllopertha horticola Species 0.000 description 1
• 241001640279 Phyllophaga Species 0.000 description 1
• 241000275067 Phyllotreta Species 0.000 description 1
• 241000437063 Phyllotreta striolata Species 0.000 description 1
• 241000233614 Phytophthora Species 0.000 description 1
• 241000690748 Piesma Species 0.000 description 1
• 238000003482 Pinner synthesis reaction Methods 0.000 description 1
• 235000016761 Piper aduncum Nutrition 0.000 description 1
• 240000003889 Piper guineense Species 0.000 description 1
• 235000017804 Piper guineense Nutrition 0.000 description 1
• 235000008184 Piper nigrum Nutrition 0.000 description 1
• 240000004713 Pisum sativum Species 0.000 description 1
• 235000010582 Pisum sativum Nutrition 0.000 description 1
• 241001281803 Plasmopara viticola Species 0.000 description 1
• 241000500437 Plutella xylostella Species 0.000 description 1
• 241001337928 Podosphaera leucotricha Species 0.000 description 1
• 239000004721 Polyphenylene oxide Substances 0.000 description 1
• 241000254101 Popillia japonica Species 0.000 description 1
• 241000193943 Pratylenchus Species 0.000 description 1
• 241000710336 Pratylenchus goodeyi Species 0.000 description 1
• 241000193960 Pratylenchus minyus Species 0.000 description 1
• 108700017836 Prophet of Pit-1 Proteins 0.000 description 1
• 102100038239 Protein Churchill Human genes 0.000 description 1
• 241000221300 Puccinia Species 0.000 description 1
• YPCALTGLHFLNGA-UHFFFAOYSA-N Pyracarbolid Chemical compound C1CCOC(C)=C1C(=O)NC1=CC=CC=C1 YPCALTGLHFLNGA-UHFFFAOYSA-N 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• 241000201375 Radopholus similis Species 0.000 description 1
• 241000590363 Reticulitermes lucifugus Species 0.000 description 1
• 241001136903 Rhagoletis pomonella Species 0.000 description 1
• 241001480837 Rhipicephalus annulatus Species 0.000 description 1
• 241000864246 Rhipicephalus decoloratus Species 0.000 description 1
• 241000238680 Rhipicephalus microplus Species 0.000 description 1
• 241001361634 Rhizoctonia Species 0.000 description 1
• 241001575051 Rhyacionia Species 0.000 description 1
• 235000004443 Ricinus communis Nutrition 0.000 description 1
• 241000710331 Rotylenchus robustus Species 0.000 description 1
• 240000000111 Saccharum officinarum Species 0.000 description 1
• 235000007201 Saccharum officinarum Nutrition 0.000 description 1
• 241001402072 Sappaphis Species 0.000 description 1
• 241000722027 Schizaphis graminum Species 0.000 description 1
• 241000343234 Scirtothrips citri Species 0.000 description 1
• 241000209056 Secale Species 0.000 description 1
• 235000007238 Secale cereale Nutrition 0.000 description 1
• 241001533598 Septoria Species 0.000 description 1
• 241000180219 Sitobion avenae Species 0.000 description 1
• 241001168723 Sitona lineatus Species 0.000 description 1
• 241000254181 Sitophilus Species 0.000 description 1
• 241000753145 Sitotroga cerealella Species 0.000 description 1
• 240000003768 Solanum lycopersicum Species 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 241000517830 Solenopsis geminata Species 0.000 description 1
• 241000736128 Solenopsis invicta Species 0.000 description 1
• 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
• 241000256248 Spodoptera Species 0.000 description 1
• 241000256247 Spodoptera exigua Species 0.000 description 1
• 241000256250 Spodoptera littoralis Species 0.000 description 1
• 241000985245 Spodoptera litura Species 0.000 description 1
• 241001161749 Stenchaetothrips biformis Species 0.000 description 1
• 241000897276 Termes Species 0.000 description 1
• 241001454293 Tetranychus urticae Species 0.000 description 1
• 241001231950 Thaumetopoea pityocampa Species 0.000 description 1
• 241000339373 Thrips palmi Species 0.000 description 1
• 241000339374 Thrips tabaci Species 0.000 description 1
• 241000051707 Thyanta perditor Species 0.000 description 1
• 240000002657 Thymus vulgaris Species 0.000 description 1
• 235000007303 Thymus vulgaris Nutrition 0.000 description 1
• 241001414989 Thysanoptera Species 0.000 description 1
• 241001240492 Tipula oleracea Species 0.000 description 1
• 241000511627 Tipula paludosa Species 0.000 description 1
• 241001271990 Tomicus piniperda Species 0.000 description 1
• 241001238452 Tortrix Species 0.000 description 1
• 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
• 241001220305 Trichodorus primitivus Species 0.000 description 1
• 241000255993 Trichoplusia ni Species 0.000 description 1
• 241001389006 Tuta absoluta Species 0.000 description 1
• 241000402796 Tylenchorhynchus claytoni Species 0.000 description 1
• 241000221566 Ustilago Species 0.000 description 1
• 241000228452 Venturia inaequalis Species 0.000 description 1
• 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
• 240000006677 Vicia faba Species 0.000 description 1
• 235000010749 Vicia faba Nutrition 0.000 description 1
• 241001274787 Viteus Species 0.000 description 1
• 240000006365 Vitis vinifera Species 0.000 description 1
• 235000014787 Vitis vinifera Nutrition 0.000 description 1
• 241001466330 Yponomeuta malinellus Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
• 241000495395 Zeiraphera canadensis Species 0.000 description 1
• 241001136529 Zeugodacus cucurbitae Species 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 238000005575 aldol reaction Methods 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 125000005108 alkenylthio group Chemical group 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000002877 alkyl aryl group Chemical group 0.000 description 1
• 150000005215 alkyl ethers Chemical class 0.000 description 1
• 125000005037 alkyl phenyl group Chemical group 0.000 description 1
• 150000008051 alkyl sulfates Chemical class 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• 230000009435 amidation Effects 0.000 description 1
• 238000007112 amidation reaction Methods 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
• 235000019289 ammonium phosphates Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
• 235000011130 ammonium sulphate Nutrition 0.000 description 1
• IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
• 150000008059 anilinopyrimidines Chemical class 0.000 description 1
• 239000010775 animal oil Substances 0.000 description 1
• 125000000129 anionic group Chemical group 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
• 239000002969 artificial stone Substances 0.000 description 1
• 125000001769 aryl amino group Chemical group 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
• RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• NBNTWDUNCHRWMT-UHFFFAOYSA-N bis(4-chlorophenyl)-pyridin-3-ylmethanol Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=NC=CC=1)(O)C1=CC=C(Cl)C=C1 NBNTWDUNCHRWMT-UHFFFAOYSA-N 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
• TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
• 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
• PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 229910052570 clay Inorganic materials 0.000 description 1
• 239000011280 coal tar Substances 0.000 description 1
• 235000008504 concentrate Nutrition 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 239000007859 condensation product Substances 0.000 description 1
• 150000001879 copper Chemical class 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 244000038559 crop plants Species 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• NUFBGJAEANEZKW-UHFFFAOYSA-N cyclopropyloxycyclopropane Chemical compound C1CC1OC1CC1 NUFBGJAEANEZKW-UHFFFAOYSA-N 0.000 description 1
• HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
• MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
• 229910000071 diazene Inorganic materials 0.000 description 1
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• CJHXCRMKMMBYJQ-UHFFFAOYSA-N dimethirimol Chemical compound CCCCC1=C(C)NC(N(C)C)=NC1=O CJHXCRMKMMBYJQ-UHFFFAOYSA-N 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 1
• WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
• 239000012990 dithiocarbamate Substances 0.000 description 1
• 150000004659 dithiocarbamates Chemical class 0.000 description 1
• JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 description 1
• 229910000514 dolomite Inorganic materials 0.000 description 1
• 239000010459 dolomite Substances 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 235000005489 dwarf bean Nutrition 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000004744 fabric Substances 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 235000013312 flour Nutrition 0.000 description 1
• MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 244000000004 fungal plant pathogen Species 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 239000003630 growth substance Substances 0.000 description 1
• 125000004997 halocarbonyl group Chemical group 0.000 description 1
• 150000002366 halogen compounds Chemical class 0.000 description 1
• 125000004475 heteroaralkyl group Chemical group 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
• 210000001320 hippocampus Anatomy 0.000 description 1
• 238000006698 hydrazinolysis reaction Methods 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
• 238000005470 impregnation Methods 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000002917 insecticide Substances 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
• PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 1
• 239000003350 kerosene Substances 0.000 description 1
• 150000004715 keto acids Chemical class 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 150000002596 lactones Chemical class 0.000 description 1
• 239000006028 limestone Substances 0.000 description 1
• 235000009973 maize Nutrition 0.000 description 1
• CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
• 238000001465 metallisation Methods 0.000 description 1
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
• RDFJFVXMRYVOAC-UHFFFAOYSA-N methiodal Chemical compound OS(=O)(=O)CI RDFJFVXMRYVOAC-UHFFFAOYSA-N 0.000 description 1
• MGUDGDSNHPKOLL-UHFFFAOYSA-N methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1=CC=CC=C1CBr MGUDGDSNHPKOLL-UHFFFAOYSA-N 0.000 description 1
• 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
• HIIRDDUVRXCDBN-OBGWFSINSA-N metominostrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1OC1=CC=CC=C1 HIIRDDUVRXCDBN-OBGWFSINSA-N 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
• JNLAWMGPPJLSMA-UHFFFAOYSA-N n-(2-iodophenyl)benzamide Chemical compound IC1=CC=CC=C1NC(=O)C1=CC=CC=C1 JNLAWMGPPJLSMA-UHFFFAOYSA-N 0.000 description 1
• BSASAHDKONAXQX-UHFFFAOYSA-N n-(2-methylphenyl)benzamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC=CC=C1 BSASAHDKONAXQX-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• KAAHHLOYOIUHHH-UHFFFAOYSA-N n-methoxyethanimine Chemical compound CON=CC KAAHHLOYOIUHHH-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 150000002828 nitro derivatives Chemical class 0.000 description 1
• SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 235000014571 nuts Nutrition 0.000 description 1
• NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
• KPTCZURLWZSRKB-UHFFFAOYSA-N o-prop-2-enylhydroxylamine Chemical compound NOCC=C KPTCZURLWZSRKB-UHFFFAOYSA-N 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
• 229960003540 oxyquinoline Drugs 0.000 description 1
• 239000000123 paper Substances 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 235000020232 peanut Nutrition 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
• 229940044654 phenolsulfonic acid Drugs 0.000 description 1
• 150000008060 phenylpyrroles Chemical class 0.000 description 1
• 150000003003 phosphines Chemical class 0.000 description 1
• XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 239000002798 polar solvent Substances 0.000 description 1
• 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
• 229920000570 polyether Polymers 0.000 description 1
• 229920000151 polyglycol Polymers 0.000 description 1
• 239000010695 polyglycol Substances 0.000 description 1
• 229920001451 polypropylene glycol Polymers 0.000 description 1
• 235000012015 potatoes Nutrition 0.000 description 1
• 235000014483 powder concentrate Nutrition 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
• ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
• MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 150000004756 silanes Chemical class 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 238000003892 spreading Methods 0.000 description 1
• 239000004575 stone Substances 0.000 description 1
• 235000021012 strawberries Nutrition 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
• YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
• QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
• 239000001585 thymus vulgaris Substances 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 238000009827 uniform distribution Methods 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000004563 wettable powder Substances 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1